721428-34-8

Basic information

• Product Name: 5-CHLOROMETHYL-3-(4-FLUORO-PHENYL)-[1,2,4]OXADIAZOLE
• Synonyms: 5-(Chloromethyl)-3-(4-fluorophenyl)-1,2,4-oxadiazole
• CAS NO: 721428-34-8
• Molecular Formula: C₉H₆ClFN₂O
• Molecular Weight: 212.61
• Mol File: 721428-34-8.mol

Chemical Properties

• Melting Point: 31-32 °C(Solv: hexane (110-54-3))
• Boiling Point: 311.5±52.0 °C(Predicted)
• Appearance: /
• Density: 1.364±0.06 g/cm3(Predicted)
• PKA: -2.57±0.37(Predicted)
• CAS DataBase Reference: 5-CHLOROMETHYL-3-(4-FLUORO-PHENYL)-[1,2,4]OXADIAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-CHLOROMETHYL-3-(4-FLUORO-PHENYL)-[1,2,4]OXADIAZOLE(721428-34-8)
• EPA Substance Registry System: 5-CHLOROMETHYL-3-(4-FLUORO-PHENYL)-[1,2,4]OXADIAZOLE(721428-34-8)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 721428-34-8(Hazardous Substances Data)

Usage

Uses

5-Chloromethyl-3-(4-fluoro-phenyl)-[1,2,4]oxadiazole

Upstream product

• 22179-78-8 4-fluoro-benzamidoxime 
• 79-04-9 chloroacetyl chloride 
• 794554-75-9 C₉H₈ClFN₂O₂ 
• 456-06-4 4-fluorobenzoyl hydrazide 
• 1194-02-1 4-fluorobenzonitrile 
• 22179-78-8 (Z)-4-fluoro-N'-hydroxybenzimidamide 
• 74974-54-2 2-chloro-1,1,1-trimethoxyethane 
• 794554-75-9 C₉H₈ClFN₂O₂ 

Downstream Products

• 1062370-79-9 C₁₇H₁₀FN₃O₃ 
• 1229114-79-7 {5-chloro-2-[(3-(4-fluorophenyl)-1,2,4-oxadiazol-5-yl)-methoxy]-phenyl}-(phenyl)-methanone 
• 937665-70-8 (3-(4-fluorophenyl)-1,2,4-oxadiazol-5-yl)methylamine 

Relevant articles and documents

In vitro anti-TB properties, in silico target validation, molecular docking and dynamics studies of substituted 1,2,4-oxadiazole analogues against Mycobacterium tuberculosis

The alarming increase in multi- and extensively drug-resistant (MDR and XDR) strains of Mycobacterium tuberculosis (MTB) has triggered the scientific community to search for novel, effective, and safer therapeutics. To this end, a series of 3,5-disubstitu

Synthesis of Some Azamacrocycles Bearing 1,2,4-Oxadiazole and 1,2,3-Triazole Moieties

Abstract: A tetraazacrown ether,4,9-di(prop-2-yn-1-yl)-1,4,9,12-tetraazacyclohexadecane-2,11-dione, bearingpropargyl groups on two nitrogens was synthesized starting from1,4,9,12-tetraazacyclohexadecane-2,11-dione and subjected to 1,3-cycloadditionreactio

Reactions of 3-(p-substituted-phenyl)-5-chloromethyl-1,2,4-oxadiazoles with KCN leading to acetonitriles and alkanes via a non-reductive decyanation pathway

The present work describes an unfamiliar reaction of 5-(chloromethyl)-3-substituted-phenyl-1,2,4-oxadiazoles with KCN affording trisubstituted 1,2,4-oxadiazol-5-ylacetonitriles and their parent alkanes, namely, 1,2,3-trisubstituted-1,2,4-oxadiazol-5-ylpro

Design, synthesis, and bioactivities of novel oxadiazole-substituted pyrazole oximes

A series of novel pyrazole oxime derivatives containing a substituted oxadiazole group were designed and synthesized. The bioassay results indicated that some title compounds displayed good acaricidal and insecticidal activities against Tetranychus cinnabarinus, Aphis medicaginis, Oriental armyworm, and Nilaparvata lugens. Especially, compounds 7a, 7b, and 7c had 80%, 90%, and 90% insecticidal activities against A. medicaginis at 20 μg/mL, respectively. Interestingly, some of the designed compounds displayed wonderful fungicidal activities in vivo against cucumber Pseudoperonospora cubensis. Furthermore, compounds 7a (EC50= 4.97 μg/mL) and 7h (EC50= 0.51 μg/mL) showed excellent fungicidal activity against P. cubensis comparable or better than that of the control Pyraclostrobin (EC50= 4.59 μg/mL).

Design, microwave assisted synthesis and characterization of substituted 1,2,4-oxadiazole analogues as promising pharmacological agents

Microwave assisted synthesis of a series of 3,5-disubstituted-1,2,4-oxadiazole analogues (3a-j) has been achieved between 5-(chloromethyl)-3-substituted phenyl-1,2,4-oxadiazoles (2a-j) and substituted benzophenone in presence of potassium carbonate in ace

Discovery and preliminary evaluation of 2-aminobenzamide and hydroxamate derivatives containing 1,2,4-oxadiazole moiety as potent histone deacetylase inhibitors

Using Entinostat as a lead compound, 2-aminobenzamide and hydroxamate derivatives have been designed and synthesized. The entire target compounds were investigated for their in vitro antiproliferative activities using the MTT-based assay against five human cancer cell lines including U937, A549, NCI-H661, MDA-MB-231 and HCT116. 2-Aminobenzamide series of compounds (10a-10j) demonstrated the most significant inhibition against human acute monocytic myeloid leukemia cell line U937, but no or poor activities against two human lung cancer cell lines. Furthermore, the target compounds were screened for their inhibitory activities against HDAC 1, 2, and 8. 2-Aminobenzamide derivatives (10) manifested a higher selectivity for HDAC 1 over HDAC 2, but were not active against HDAC 8. In contrast, most hydroxamate derivatives (11) inhibit HDAC 8 with lower IC50 values than SAHA and Entinostat. Docking study with selected compounds 10f and 11a revealed that the compounds might bind tightly to the binding pockets in HDAC 2 and HDAC 8, respectively. The results suggest that they may be promising lead compounds for the development of novel anti-tumor drug potentially via inhibiting HDACs.

Synthesis of novel triazoles bearing 1,2,4-oxadiazole and phenylsulfonyl groups by 1,3-dipolar cycloaddition of some organic azides and their biological activities

1,3-Dipolar cycloaddition of 5-azidomethyl-3-p-substituted phenyl-1,2,4-oxadiazoles to phenyl vinyl sulfone and bismaleimide gives rise straightforwardly to 1-((3-(p-substituted) phenyl-1,2,4-oxadiazol-5-yl)methyl)-4-(phenylsulfonyl)-4,5-dihydro-1H-1,2,3-triazoles and bisdihydropyrrolo[3,4-d][1,2,3]triazole-4,6(3aH,5H)-diones. The structures of the new cycloadducts were elucidated by means of IR, NMR (1H, 13C, 2D), mass spectra, and physical characteristics (mp and Rfvalues). In addition, anticancer activities of the cycloadducts against MCF-7 cells were also investigated.

Synthesis and anti-protozoal activity of novel dihydropyrrolo[3,4-d][1,2,3] triazoles

1,2,4-Oxadiazole and 1,2,3-triazole containing heterocyclic compounds continue to gain interest in synthesis of chemical entities and exhibit various biological activities as anti-protozoal and anti-cancer agents. By using the principle of bioisosterism,

Design, synthesis, characterization, and antibacterial activity of {5-chloro-2-[(3-substitutedphenyl-1,2,4-oxadiazol-5-yl)-methoxy]-phenyl} -(phenyl)-methanones

In the present investigation, a series of novel {5-chloro-2-[(3-(substitutedphenyl)-1,2,4-oxadiazol-5-yl)-methoxy]-pheny l}-(phenyl)-methanones (3a-i) have been synthesized from 5-(chloromethyl)-3-substitutedphenyl-1,2,4-oxadiazole (2a-i). The newly synth

Design, synthesis, and biological activities of novel 2-cyanoacrylates containing oxazole, oxadiazole, or quinoline moieties

A series of novel 2-cyanoacrylates containing an oxazole, oxadiazole, or quinoline moiety were designed and synthesized, and their structures were characterized by 1H NMR and elemental analysis (or high-resolution mass spectrometry). Their herbicidal activities against four weeds were evaluated, and the result indicated that some of the title compounds showed excellent herbicidal activities against rape and amaranth pigweed in postemergence treatment at a dose of 375 g/ha. Furthermore, most of these cyanoacrylates exhibited interesting plant growth regulatory activities.